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Stictic Acid

(Synonyms: NSC 87511) 目录号 : GC44955

A depsidone

Stictic Acid Chemical Structure

Cas No.:549-06-4

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500μg
¥2,038.00
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2.5mg
¥9,181.00
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产品描述

Stictic acid is a depsidone found in lichen. It preferentially inhibits growth of HT-29 human colon adenocarcinoma cells over non-malignant cells (IC50s = 29.29 and 2,478.4 µg/ml, respectively).

Chemical Properties

Cas No. 549-06-4 SDF
别名 NSC 87511
Canonical SMILES COC1=CC(C)=C(C(OC(C(C)=C(O)C2=C3C(O)OC2=O)=C3O4)=O)C4=C1C=O
分子式 C19H14O9 分子量 386.3
溶解度 DMF: Soluble,DMSO: Soluble,Ethanol: Soluble,Methanol: Soluble 储存条件 Store at -20°C
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5 mM 0.5177 mL 2.5887 mL 5.1773 mL
10 mM 0.2589 mL 1.2943 mL 2.5887 mL
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Research Update

NMR reassignment of Stictic Acid isolated from a Sumatran lichen Stereocaulon montagneanum (Stereocaulaceae) with superoxide anion scavenging activities

Z Naturforsch C J Biosci 2017 Jan 1;72(1-2):55-62.PMID:27770605DOI:10.1515/znc-2016-0148.

The phytochemical study of Stereocaulon montagneanum harvested in Sumatra (Indonesia) led to the isolation of 11 known compounds including two metabolites not previously described in the genus Stereocaulon, peristictic acid (8) and menegazziaic acid (10). The complete 1H and 13C NMR spectral assignments of Stictic Acid derivatives are reported with some revisions. Five depsidones belonging to the Stictic Acid chemosyndrome were superoxide anion scavengers as potent as ascorbic acid and with no toxicity on two human cell lines.

Stictic Acid derivatives from the lichen Usnea articulata and their antioxidant activities

J Nat Prod 2007 Jul;70(7):1218-20.PMID:17629329DOI:10.1021/np070145k.

Two new beta-orcinol depsidones, 1 and 2, together with 13 known compounds were isolated from the lichen Usnea articulata. The structures of 1 and 2 were elucidated by spectroscopic analyses and those of known compounds by comparison of their spectroscopic data with literature values or by direct comparison with authentic standards. Compounds 1, 2, and 5 exhibited moderate antiradical activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. The depsidones 4 and 5 showed better superoxide anion scavenging activity (IC50 = 566 and 580 microM, respectively) than quercetin (IC50 = 754 microM).

A Review of Anti-Cancer and Related Properties of Lichen-Extracts and Metabolites

Anticancer Agents Med Chem 2022;22(1):115-142.PMID:34225637DOI:10.2174/1871520621666210322094647.

Background: Lichens are a composite consortium of a fungus and an alga. The symbiotic organisms are naturally equipped with distinct characteristics as compared to constituting organisms separately. Lichens, due to their peculiar anatomy and physiology, are the reservoir of more than 600 unique secondary metabolites, also known as 'lichen substances'. Since ancient times, many ethnic groups from various parts of the world have known about the applications of lichens as major provenance of food/fodder, medicine, dyes, spices, perfumes, etc. Lichen substances have shown impressive antioxidant, antimicrobial, antiviral, anti-tumor, and antiinflammatory activities under experimental conditions. Usnic acid, a well-known metabolite found in several species of lichens, possesses potent antioxidant and anti-inflammatory activities. It also has significant antiproliferative potential, as revealed through testing in different cancer cell lines. Atranorin, Lecanoric acid, Norstictic acid, Lobaric acid, Stictic Acid, Ramalin, Gyrophoric acid, Salazinic acid, Protolichesterinic, and Fumarprotocetraric acid are some of the other purified lichen-metabolites with potent anti-cancer activities. Objective: This study presents an overview of lichen-derived extracts and compounds showing anti-cancer (or related) properties. Method: The review comprehends different studies (in vivo and in vitro) backing up the possibility of lichenextracts and metabolites towards their use as antioxidant, anti-proliferative, anti-inflammatory, and Epithelialmesenchymal transition (EMT) -inhibiting agents. Results: Various studies carried out to date show that lichen-extracts and metabolites have a range of anti-cancer and related properties that include anti-oxidative, anti-inflammatory, anti-proliferative, pro-apoptotic, and the potential of inhibition of cancer-associated EMT that is responsible for drug resistance and metastasis of cancer cells in a substantial proportion of cases. Conclusion: Lichens are the repertoire of a plethora of lichen-metabolites with significant anti-cancer potential. However, some of the critical 'anti-cancer related' properties, such as the ability of EMT-inhibition and the potential of induction of apoptosis, are relatively less studied for several lichen compounds. Additionally, many lichen compounds need to be purified at a larger scale to explore their anti-cancer potential.

Lichen Depsidones with Biological Interest

Planta Med 2022 Sep;88(11):855-880.PMID:34034351DOI:10.1055/a-1482-6381.

Depsidones are some of the most abundant secondary metabolites produced by lichens. These compounds have aroused great pharmacological interest due to their activities as antioxidants, antimicrobial, and cytotoxic agents. Hence, this paper aims to provide up-to-date knowledge including an overview of the potential biological interest of lichen depsidones. So far, the most studied depsidones are fumarprotocetraric acid, lobaric acid, norstictic acid, physodic acid, salazinic acid, and Stictic Acid. Their pharmacological activities have been mainly investigated in in vitro studies and, to a lesser extent, in in vivo studies. No clinical trials have been performed yet. Depsidones are promising cytotoxic agents that act against different cell lines of animal and human origin. Moreover, these compounds have shown antimicrobial activity against both Gram-positive and Gram-negative bacteria and fungi, mainly Candida spp. Furthermore, depsidones have antioxidant properties as revealed in oxidative stress in vitro and in vivo models. Future research should be focused on further investigating the mechanism of action of depsidones and in evaluating new potential actions as well as other depsidones that have not been studied yet from a pharmacological perspective. Likewise, more in vivo studies are prerequisite, and clinical trials for the most promising depsidones are encouraged.

Phytochemical Composition of Lichen Parmotrema hypoleucinum (J. Steiner) Hale from Algeria

Molecules 2022 Aug 16;27(16):5229.PMID:36014465DOI:10.3390/molecules27165229.

In this work, we carried out studies of the chemical composition of hexane, chloroform and ethanol extracts from two samples of the lichen Parmotrema hypoleucinum collected in Algeria. Each sample of the lichen P. hypoleucinum was collected on two different supports: Olea europaea and Quercus coccifera. Hexane extracts were prepared, in Soxhlet; each hexane extract was fractionated by its solubility in methanol; the products soluble in methanol were separated (cold): 1-Hexane, 2-Hexane; and the products insoluble in methanol (cold): 1-Cires, 2-Cires. A diazomethane esterified sample of 1-Hexane, 2-Hexane, 1-Cires and 2-Cires was analyzed by GC-MS, and the components were identified as methyl esters. In the 1-Hexane and 2-Hexane fractions, the methyl esters of the predominant fatty acids in the lichen were identified: palmitic acid, linoleic acid, oleic acid and stearic acid; a hydrocarbon was also identified: 13-methyl-17-norkaur-15-ene and several derivatives of orsellinic acid. In the 1-Cires and 2-Cires fractions, the previous fatty acids were no longer observed, and only the derivatives of orsellinic acid were found. The analysis of the 1-Hexane, 2-Hexane fractions by HPLC-MS/MS allows us to identify different chemical components, and the most characteristic products of the lichen were identified, such as Atranol, Chloroatranol, Atranorin and Chloroatranorin. In the fractions of 1-Cires and 2-Cires, the HPLC-MS/MS analysis reveals that they are very similar in their chemical components; the characteristic products of this lichen in this fraction are Atranorin and Chloroatranorin. In the extracts of chloroform, 1-Chloroform and 2-Chloroform, the analysis carried out by HPLC-MS/MS shows small differences in their chemical composition at the level of secondary products; among the products to be highlighted for this work, we have chloroatranorin, the Stictic Acid, norstictic acid and other derivatives. In the analysis of the most polar extracts carried out in ethanol: 1-Ethanol and 2-Ethanol, HPLC-MS/MS analysis shows very similar chemical compositions in these two extracts with small differences. In these extracts, the following acids were identified as characteristic compounds of this lichen: constictic acid, Stictic Acid, substictic acid and methylstictic acid. In the HPLC-MS/MS analysis of all these extracts, alectoronic acid was not found.